NCAA Tournament Pitfalls to Avoid

At this point, many of you have already filled out your NCAA March Madness brackets for a pool with coworkers or classmates. Even if you haven't seen a basketball game all year, it makes the first weekend of the tournament exciting to have your five dollars riding on the outcome of so many games, and after all, the pool winner usually isn't one of the rabid sports fans in the office. There can be a downside to this seemingly harmless fun, though. Here are a few pitfalls to avoid while betting on the tournament.

Don't Short Kansas

Commodities traders have long used a more sophisticated way to gamble on the tournament than the standard old paper bracket pool. Instead, they treat each team's tournament chances as tradable commodities that they can then buy, sell, and short according to their hunches. As a team's perceived road to the championship gets easier due to upsets or tougher due to injuries, the prices of each team's shares fluctuate accordingly. The eventual champion's shares are all worth some predetermined amount, usually $100.

While a bad opening weekend can't wipe you for the entire tournament out like it does in a standard bracket pool, these systems also lack the whole "put in your five dollars, then sit back and watch" safeguard on your wallet. At various points, the ability to keep buying in has led to some serious debacles. In 1991 a clerical assistant at Paine Webber had a strong feeling that Duke was about to go belly-up and kept shorting the Blue Devils. If you thought Kentucky fans were the only ones who hurt after Christian Laettner's miracle shot to send Duke to the Final Four and their eventual championship, think again; this young clerk lost $330,000 and his job. Another clerk supposedly lost $200,000 trying the same trick with Kentucky during their title campaign in 1996.

Try to Keep Your Job

Everyone loves a good office pool, right? Maybe not. According to a 2006 estimate by consultants at Challenger, Gray, & Christmas, the tournament costs employers upwards of $3.8 billion in lost productivity. While the accuracy of this figure is certainly debatable, it's hard to argue that anyone's more productive while checking four scoreboard tabs every fifteen seconds and then cross-referencing them against their brackets.

Some companies have taken strikingly firm stances against pools. In 1997 Fidelity Investments fired nine employees and disciplined 16 more for participating in football and basketball pools via office email. No word on whether or not Fidelity was just being reasonable; does an investment firm really need someone who picks a 16 seed to win a first-round game every year?

No, Really, Try to Keep Your Job

In 2003, Rick Neuheisel was the successful young coach of the University of Washington's football team. He'd also received some nice little bumps to his income the previous two years when he pocketed some serious cash in a neighborhood March Madness pool. Participants in Neuheisel's pool picked single teams rather than filling out brackets, and when Maryland won the title in 2002, Neuheisel's $7,000 bid for the Terrapins' rights in the pool returned over $25,000. Even better, the University of Washington had explicitly told him in a memo that off-campus pools like this were kosher with the NCAA.

Whoops! Turns out the pools weren't legal with the NCAA, and the Huskies' compliance office had given Neuheisel some bad information. When Neuheisel wasn't forthcoming with investigators, the school fired him for participating in the pools, and he went from golden boy coach of a Pac-10 power to volunteer coach at a local high school.

In the end, things turned out okay for Neuheisel, though. Since Washington had told him it was okay to enter the pool, he ended up winning a $4.5 million settlement against the school and the NCAA. After a stint as quarterbacks coach for the Ravens, Neuheisel recently got a new head-coaching gig at his alma mater, UCLA, a conference rival of the Washington Huskies.

Don't Ruin It for Everyone

Part of the allure of winning a pool is that your income will be tax-free, right? You get an envelope of cash the government doesn't know about, and you can spend it on whatever whim you'd like. That used to be true of the March Madness pool at Jody's Club Forest in Staten Island, an annual event that drew throngs of bettors to line up outside the tavern to enter a bracket. The pool, which opened in 1977, cost $10 to enter. In 2006, the pot was $1.5 million.

The pool was technically legal since Jody's wasn't taking any money out of the pot for running the pool, but one winner started to muck things up by filing his winnings with the IRS. Apparently such a large windfall attracted unwanted IRS scrutiny for other recent winners as well as the bar itself. As a result, the pool has been on hiatus for the last two years.

Ethan Trex grew up idolizing Vince Coleman, and he kind of still does. Ethan co-writes Straight Cash, Homey, the Internet's undisputed top source for pictures of people in Ryan Leaf jerseys.